The Indian presence in Ethiopia has attracted little attention in Ethiopian historiography. Yet Indian businessmen were as instrumental to Ethiopia’s early 20th century economy as they were in British East Africa at the same period. As part of a broader research project aimed at addressing this gap, this article explores the life and achievements of Mohamedally Shaikh Sharafaly, the best known of these Indian businessmen, who set up one of the largest commercial and industrial businesses in Ethiopia. The account follows the narrative of an un-published letter the merchant wrote in 1940 about his business trajectory. From his arrival in Harar in the late 19th century to the eventual expulsion of his company in 1937, his story is highly revealing of the political context in which large foreign businesses would emerge, involving both friendship with the Ethiopian emperors and diplomatic protection, in the case of Indians as British subjects. Mohamedally Shaikh Sharafaly created an extensive network of Indian outlets throughout the country and organized a powerful multi-partnershipwith Indian fellows, with branches in Djibouti, Aden, and Berbera. The G. M. Mohamedally & Co was much more than a mere business. On several occasions, the company provided intelligence to foreign countries and it actively supported Ethiopians against the Italian occupation. On the social scene, it remained a long-term leader of the Indian community and was famous for its various philanthropic engagements. The 1937 expulsion, as brutal as it was, also showed the political power exercised in India by the company and its founder.